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■ Rapid ‘SAR’ via Click Chemistry: An Alkyne-Bearing Spiramycin is fused with Diverse Azides to Yield New Triazole-Antibacterial Candidates

Tomoyasu Hirose, Toshiaki Sunazuka, Yoshihiko Noguchi, Yukie Yamaguchi, Hideaki Hanaki, K. Barry Sharpless, and Satoshi Omura*

*Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642,

Abstract

The spiramycin analogue, 2’-acetyl-4’’’-de-N-methyl-4’’-O-t- butyldimethylsilylspiramycin I 3,18-(O-t-butyldimethylsilyl)acetal(1), was found to be an adequate antibacterial agent against MRSA strains. An acetylenic sidechain was attached to 1 producing the analog (8), with the core intact but displaying a tethered terminal alkyne, ready for reaction with 19 diverse azides. In the event, the copper-catalyzed Fokin-Huisgen triazole synthesis/coupling gave each of the nineteen new 4’’-O-acyl triazole derivatives of 1 in good to nearly quantitative isolated yields.